ES2562854T3 - Use of isosorbide monoesters as fungicidal active products - Google Patents

Abstract

Use of one or more of the compounds of the formula (I) ** Formula ** where R is a linear or branched alkyl group with 5 to 11 carbon atoms, or a linear or branched, mono- or polyunsaturated alkenyl group, with 5 to 11 carbon atoms, as a fungicide.

Description

DESCRIPTION

Use of isosorbide monosteres as fungicidal active products

The present invention relates to the use of isosorbide monosters as a fungicide.

In the industry, preservatives or biocides are used to protect products, such as, for example, cosmetic, dermatological or pharmaceutical compositions, phytosanitary formulations, washing or cleaning agents, or dyes or paints, against microbial attack. Numerous preservative agents are known for this purpose. By way of example, preservatives of Annex V of the EU cosmetics standard or biocides of the EU biocides standard can be used for this purpose.

However, in the use of many preservative agents it is disadvantageous that their obtaining is frequently expensive and is based on synthetic raw materials. In addition, its preservative action often requires improvement, so that high concentrations of employment are necessary for sufficient preservation.

Therefore, there was the task of making available antimicrobial active products, which have an advantageous yield as a preservative agent, and in addition they are distinguished by the advantage of being based on regenerative raw materials.

Surprisingly, it was now discovered that this problem is solved by compounds of the formula (I)

image 1

where

R is a linear or branched alkyl group with 5 to 11, preferably 7 to 9, and especially preferably 7 carbon atoms, or a linear or branched, mono- or polyunsaturated alkenyl group, with 5 to 11, preferably 7 to 9, and especially preferably 7 carbon atoms.

Therefore, the use of one or more compounds of the formula (I) is the subject of the invention.

image2

where

R is a linear or branched alkyl group with 5 to 11, preferably 7 to 9, and particularly preferably 7 carbon atoms, or a linear or branched, mono or polyunsaturated alkenyl group, with 5 to 11, preferably 7 to 9 , and especially preferably 7 carbon atoms, as a fungicide.

The compounds of the formula (I) have very good performance as preservatives and are suitable for use as fungicides. They are also based on regenerative raw materials.

In comparison with the use of organic acids as preservatives, the compounds of the formula (I) also have the advantage of an efficacy over a wider pH value range. While organic acids frequently show a good action only in the pH range of 3.5 to 6, the compounds of formula (I) can advantageously also be used at higher pH values.

Compositions that are at least partially based on regenerative raw materials and can be used as preservatives are already known.

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Document DE 10 2009 022 444 (Clariant) describes liquid compositions containing sorbitan monocaprylate and antimicrobial active products, such as special organic acids and their salts, special formaldehyde donors, special isothiazolinones, special paraben esters and their salts, and Special pyridones and their salts, as well as their use for the preservation of cosmetic, dermatological or pharmaceutical products.

In DE 10 2009 022 445 (Clariant) liquid compositions containing sorbitan and alcohol monocaprylate and their use for the preservation of cosmetic, dermatological or pharmaceutical products are disclosed.

JP 8187070 (A) (Lion) discloses a mixture of Ca-Cia fatty acid monoster esters, and at least one polyol selected from sorbitol, 1,5-sorbitan, 1,4- sorbitan and isosorbide, and fatty acid diesters of these fatty acids and polyols in a weight ratio of monoster: diester of 33: 7 to 9: 1 as an antimicrobial active product against bacteria for food products or beverages.

The compounds of the formula (I) can be obtained, for example, according to methods of common use for the specialist. By way of example, the compounds of the formula (I) can be obtained by esterification of isosorbide according to customary methods known to the specialist, being in turn both the isosorbide itself, as well as the acidic components used for esterification.

The compound or compounds of the formula (I) are used as a fungicide. In the scope of the present invention, this means that the compound or compounds of the formula (I) can preferably be used as an antimicrobial active product against yeasts and fungi. The compound or compounds of the formula (I) are used especially preferably as an antimicrobial active product against fungi.

The R moiety is preferably a saturated linear alkyl moiety with 7 to 9 carbon atoms in the compound or compounds of the formula (I). Especially preferably, the R moiety in the compound or compounds of the formula (I) is a linear alkyl moiety saturated with 7 carbon atoms.

According to the invention, the compound or compounds of the formula (I) can be used as a fungicide separately or in compositions containing one or several different substances. These compositions are referred to as "compositions A" below.

In a preferred embodiment of the invention, compositions A contain one or more compounds of the formula (I), and additionally one or several different substances selected from the group consisting of sorbitol, sorbitol esters (in the case of esters sorbitol can be treated as mono-, di-, tri-, tetra-, penta- and / or hexaesters), sorbitan, sorbitan esters (in the case of sorbitan esters it can be treated as mono-, di-, tri - and / or tetraesters), isosorbide, isosorbide diesters and carboxylic acids. In the case of "sorbitan" it can be treated, for example, by 1,4- or 1,5-sorbitan. Both the carboxylic acids themselves, as well as the carboxylic acids that serve as the basis for the acidic components of said esters, correspond to the RCOOH formula, where R has the meaning indicated in the formula (I), and is preferably a linear alkyl moiety saturated with 7 carbon atoms, that is, the RCOOH carboxylic acid is preferably caprylic acid.

In a particularly preferred embodiment of the invention, compositions A contain one or more compounds of the formula (I), and additionally

I) isosorbide and

II) one or more isosorbide diesters of the formula (II)

image3

where R has the meaning indicated in formula (I), and is the isosorbide diester preferably isosorbide dicaprilate.

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Four. Five

fifty

Among these, the aforementioned compositions A also preferably contain one or more compounds of the formula (I), and additionally

I) 0.05 to 0.7, preferably 0.1 to 0.7, and especially preferably 0.2 to 0.5 parts by weight of isosorbide, and

II) 0.1 to 1.0, preferably 0.2 to 1.0, and particularly preferably 0.4 to 0.8 parts by weight of one or more isosorbide diesters of the formula (II), the isosorbide diester preferably isosorbide dicaprilate,

respectively referred to 1.0 part by weight of the compound or compounds of the formula (I), and preferably referred to 1.0 part by weight of isosorbide monocaprylate.

In a manner, in turn preferred among these, of execution of the invention, the aforementioned compositions A also do not contain RCOOH carboxylic acid, or contain up to 0.1, preferably 0.001 to 0.05, and especially preferably 0.002 to 0 , 01 parts by weight of carboxylic acid RCOOH, R having the meaning indicated above in the formula (I), and the carboxylic acid being preferably caprylic acid, referred to 1.0 part by weight of one or more compounds of the formula (I ), and preferably referred to 1.0 part by weight of isosorbide monocaprylate.

In another especially preferred embodiment of the invention, compositions A contain one or more compounds of the formula (I) and one or more sorbitan esters consisting of sorbitan and RaCOOH carboxylic acids, preferably selected from sorbitan esters constituted by 1,4- and / or

I, 5-sorbitan and RaCOOH carboxylic acids, Ra being a linear or branched alkyl group, saturated, with 5 a

II, preferably 7 to 9, and particularly preferably 7 carbon atoms, or a linear or branched, mono- or polyunsaturated alkenyl group, with 5 to 11, preferably 7 to 9, and particularly preferably 7 carbon atoms, and the weight ratio of the compound or compounds of the formula (I) being relative to the sorbitan ester or sorbitan esters also mentioned from 70: 30 to 100: 0, preferably from 80: 20 to 100: 0, so especially preferred from 90: 10 to 100: 0, and especially preferably from 95: 5 to 100: 0. The indicated weight ratio of "100: 0" means that compositions A, also mentioned, must not contain any sorbitan esters in this especially preferred form of execution of the invention.

Among the aforementioned compositions A, those where the sorbitan ester or esters constituted by sorbitan and RaCOOH carboxylic acids are selected are selected from sorbitan esters constituted by sorbitan and caprylic acid, and are preferably selected from sorbitan esters constituted by 1,4- and / or 1,5-sorbitan and caprylic acid, and the sorbitan ester is sorbitan monocaprylate, particularly preferably.

In these compositions A, the OH index of the mixture of the compound or compounds of the formula (I) and the sorbitan ester or the sorbitan esters (contained in the given case), constituted by sorbitan and RaCOOH carboxylic acids, is preferably less than or equal to 320, especially preferably less than or equal to 285, especially preferably less than or equal to 245, and extraordinarily preferably less than or equal to 225.

In another especially preferred embodiment of the invention, the OH index of the mixture of the compound or compounds of the formula (I), and the compound or compounds selected from the group consisting of sorbitol, sorbitol esters, sorbitan , esters of sorbitan, isosorbide, isosorbide diesters and carboxylic acids in compositions A, is less than or equal to 320, preferably less than or equal to 285, especially preferably less than or equal to 245, and especially preferably less than or equal to 225.

In another especially preferred embodiment of the invention, compositions A do not contain compounds selected from sorbitol and sorbitol esters.

In another especially preferred embodiment of the invention, compositions A do not contain compounds selected from sorbitan and sorbitan esters.

While compositions A contain one or more compounds selected from sorbitol and sorbitol esters (the carboxylic acid serving as the base of the acid component of these esters preferably caprylic acid), these compounds are contained in compositions A together, of preferably, in an amount less than or equal to 5.0% by weight, especially preferably in an amount less than or equal to 3.0% by weight, especially preferably in an amount less than or equal to 1, 0% by weight, and extraordinarily preferably in an amount less than or equal to 0.5% by weight,

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referring the data in% by weight respectively to the total weight of the finished compositions A.

As long as the compositions A contain one or more compounds selected from sorbitan and sorbitan esters (the carboxylic acid serving as the basis for the acid component of these esters preferably caprylic acid), these compounds are contained together, so preferably, in an amount less than or equal to 20.0% by weight, especially preferably in an amount less than or equal to 10.0% by weight, especially preferably in an amount less than or equal to 5.0 % by weight, and extraordinarily preferably in an amount less than or equal to 1.0% by weight in compositions A, the data in% by weight referring respectively to the total weight of the finished compositions A.

In another especially preferred embodiment of the invention, compositions A contain the compound or compounds of the formula (I) in amounts of at least 30% by weight, preferably in amounts of at least 50% by weight, and especially preferably in amounts of at least 60% by weight, based respectively on the total weight of the finished compositions A.

A hydroxyl index or OH of a substance is understood as that amount of KOH in mg that is equivalent to the amount of acetic acid bound in the acetylation of 1 g of substance.

Appropriate determination methods for calculating the OH index are, for example, DGF C-V 17 to (53), Ph. Eur. 2.5.3 Method A and DIN 53240.

In the scope of the present invention, the OH indices are determined in accordance with DIN 53240-2. In this case, proceed as follows: exactly 1 g is weighed on 0.1 mg of the homogenized sample to be measured. Add 20.00 ml of acetylation mixture (mixture of acetylation: 50 ml of acetic acid anhydride are introduced with stirring in 1 liter of pyridine). The sample is completely dissolved in the acetylation mixture, if necessary under stirring and heating. 5 ml of catalyst solution are added (catalyst solution: 2 g of 4-dimethylaminopyridine are dissolved in 100 ml of pyridine). The reaction vessel is closed and placed 10 minutes in the preheated water bath at 55 ° C, and in this case it is mixed. The reaction solution is then mixed with 10 ml of completely desalinated water, the reaction vessel is closed again, and allowed to react again for 10 minutes in a bath of stirred water. The sample is cooled to room temperature (25 ° C). Then 50 ml of 2- propanol and 2 drops of phenolphthalema are added. This solution is titrated with sodium hydroxide (sodium hydroxide c = 0.5 mol / l) (Va). Under the same conditions, but without sample weighing, the effective value of the acetylation mixture (Vb) is determined.

From the consumption of the determination of the effective value and the titration of the sample, the OH (OHZ) index is calculated according to the following formula:

image4

OHZ = hydroxyl content in mg of KOH / g of substance,

Va = consumption of sodium hydroxide in ml in the titration of the sample,

Vb = consumption of sodium hydroxide in ml in the titration of the effective value,

c = concentration of amounts of sodium hydroxide substance in mol / l, t = title of sodium hydroxide,

M = molar mass of KOH = 56.11 g / mol,

E = sample weight in g.

(Va-Vb) is that amount of sodium hydroxide used in ml, which is equivalent to the amount of acetic acid bound in the acetylation of the sample to be measured described above.

The method for determining the OH index, also described, is referred to below as the "OHZ-A method".

The use according to the invention preferably takes place in cosmetic, dermatological or

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pharmaceuticals, in phytosanitary formulations, in washing or cleaning agents or in dyes or paints. Phytosanitary agents preferably contain one or more pesticides.

Cosmetic, dermatological or pharmaceutical compositions, phytosanitary formulations, washing or cleaning agents, or dyes or paints, contain the compound or compounds of formula (I) 5 preferably in amounts of 0.01 to 10 , 0% by weight, especially preferably in amounts of 0.1 to 5.0% by weight, and especially preferably in amounts of 0.2 to 3.0% by weight, respectively based on weight total of the finished cosmetic, dermatological or pharmaceutical compositions, phytosanitary formulations, washing or cleaning agents or dyes or paints.

Cosmetic, dermatological or pharmaceutical compositions, phytosanitary formulations, washing or cleaning agents or dyes or paints have viscosities preferably in the range of 50 to 200,000 mPa.s, especially preferably in the range of 500 to 100 000 mPa.s, especially preferably in the range of 2,000 to 50,000 mPa.s, and particularly preferably in the range of 5,000 to 30,000 mPa.s (20 ° C, Brookfield RVT, spindle set RV at 20 revolutions per minute).

Cosmetic, dermatological or pharmaceutical compositions are preferably in the form of fluids, gels, foams, sprays, lotions or creams.

In the case of cosmetic, dermatological or pharmaceutical compositions, these are preferably agents for the treatment of athlete's foot or anti-dandruff agents. The use according to the invention takes place as a fungicide against athlete's foot and against dandruff in these cases.

Cosmetic, dermatological or pharmaceutical compositions, phytosanitary formulations, washing or cleaning agents or dyes or paints are preferably constituted on an aqueous or aqueous-alcoholic basis, or are presented as emulsions or dispersions. Especially preferably they are presented as emulsions, and in particular they are presented as oil-in-water emulsions.

Cosmetic, dermatological or pharmaceutical compositions, phytosanitary formulations, washing or cleaning agents, or dyes or paints, may contain as additional auxiliary agents and additives all the substances commonly used for the respective application, by way of example oils , waxes, emulsifiers, co-emulsifiers, dispersants, surfactants, defoamers, solubilizers, electrolytes, hydroxyacids, stabilizers, polymers, filmogens, thickeners, gelling agents, super-greasing agents, re-greasers, other antimicrobial active products, biogenic active products, astringent substances active agents, deodorants, antisolar agents, antioxidants, oxidizing agents, wetting agents, solvents, dyes, pigments, pearly shine agents, perfumes, opacifying agents and / or silicones.

Cosmetic, dermatological or pharmaceutical compositions, phytosanitary formulations, washing or cleaning agents, or dyes or paints, have pH values preferably from 2 to 11, especially preferably from 4.5 to 8.5, and especially preferably from 5.5 to 6.5.

35 The following examples and applications should explain the invention in more detail, but not limited thereto. In the case of all percentage data, it is% by weight (% by weight), as long as the opposite is not explicitly stated.

Comparative examples

A) Obtaining isosorbide caprylate

40 In an agitation apparatus with a superimposed distillation piece, 190.0 g (1.3 mol) of isosorbide (“Sorbon” from Ecogreen Oleochemicals) and 187.5 g (1.3 mol) of octanoic acid (caprylic acid) are placed ) at 80 ° C together with 0.38 g of sodium hydroxide (18% by weight, aqueous), as catalyst. Under stirring and passage of nitrogen (10-12 liters per hour) the reaction mixture was heated first to 180 ° C, beginning to distill the reaction water. The charge is then heated 1 hour at 190 ° C and in another 2 hours at 210 ° C. Once 45 210 ° C is reached, it is esterified until an acid value of <1 mg of KOH / g has been reached. 345.7 g of

amber colored isosorbide caprylate (97% of the theone). The pH value (5% by weight in ethanol / water 1: 1) amounts to 5.9. The pH value was measured according to DIN EN 1262.

Other characteristic characteristics of isosorbide caprilat:

Acid index: 0.9 mg KOH / g, measured according to DIN EN ISO 2114,

^ Hydroxyl Index: Saponification Index: Isosorbide Caprylate

206 mg of KOH / g, measured in accordance with DIN 53240-2 according to OHZ-A method, 204 mg of KOH / g, measured according to DIN EN ISO 3681. It has the following composition:

 Substance

 % in weigh

 Caprylic acid

 0.4

 Isosorbide

 18.1

 Isosorbide Monocaprylate

 50.9

 Isosorbide Dicaprilate

 30.6

5 This composition is referred to below as "isosorbide caprylate 1).

B) Determination of the antimicrobial efficacy of isosorbide caprylate 1

The antimicrobial efficacy of isosorbide caprylate 1 in butyl polyglycol against bacteria, fungi and yeasts is investigated below. For the test with bacteria, isosorbide caprylate 1 was diluted with butyl polyglycol and then added to case-agar (casema-peptone-agar), buffered at pH 7 (+/- 0.2) at 50 ° C in 10 different concentrations (then called compositions B1, B2, etc.). For the fungal and yeast assay, isosorbide caprylate 1 was diluted with butyl polyglycol, and then liquid Sabouraud-4% -dextrose agar was added, buffered to pH 5.6 (+/- 0.2) in different concentrations (a continuation called compositions PH1, PH2, etc.). Each of the compositions B1, B2, etc, or PH1, PH2, etc., was poured into Petri dishes, and inoculated respectively with the same amount of bacteria, fungi and yeasts. The minimum inhibition concentration (MHK) is the concentration at which there is an inhibition of the growth of bacteria, fungi and yeasts in the compositions B1, B2, etc., or PH1, PH2, etc.

The values determined and indicated in Table 1 below for the minimum inhibition concentrations of isosorbide caprylate 1 are already corrected in the dilution effect of butyl polyglycol.

Table 1: mmimal inhibition concentrations (MHK) of isosorbide caprylate 1

 Bacteria (B), fungi (P) or yeast (H) investigated

 MHK of isosorbide caprylate 1 [ppm]

 Staphylococcus aureus (B)

 2500

 Pseudomonas aeruginosa (B)

 10000

 Escherichia coli (B)

 7500

 Enterobacter aerogenes (B)

 10000

 Klebsiella pneumoniae (B)

 10000

 Proteus vulgaris (B)

 5000

 Pseudomonas oleovorans (B)

 10000

 Citrobacter freundii (B)

 10000

 Bacteria (B), fungi (P) or yeast (H) investigated

 MHK of isosorbide caprylate 1 [ppm]

 Candida albicans (H)

 600

 Aspergillus brasiliensis (P)

 800

 Penicillium minioluteum (P)

 600

 Aspergillus terreus (P)

 600

 Fusarium solani (P)

 600

 Penicillium funicolosium (P)

 400

The results indicated in Table 1 identify that isosorbide caprylate 1 has an antimicrobial efficacy, especially against Candida albicans yeasts and the fungi tested.

C) Antimicrobial efficacy of components of isosorbide caprylate 1

5 Caprylic acid has an antimicrobial efficacy. However, since caprylic acid is present in the composition „isosorbide caprylate 1“ only by 0.4% by weight, its antimicrobial efficacy in this composition is negligibly reduced. In addition, caprylic acid does not have an antimicrobial efficacy at pH values of 6 or more.

Analogously to the determination of the antimicrobial efficacy of isosorbide caprylate 1, in series of additional trials 10 the antimicrobial efficacy of a mixture containing 89.6% by weight of isosorbide dicaprilate and 9.4% by weight of isosorbide monocaprylate (rest: 1% by weight) (then called "isosorbide dicaprilate") on the one hand, and pure isosorbide on the other hand. The results are shown in Table 2.

Table 2: mmimal inhibition concentrations (MHK) of isosorbide and isosorbica dicaprilate

 Bacteria (B), fungi (P) or yeast (H) investigated

 MHK of isosorbide dicaprilate [ppm] MHK of isosorbide [ppm]

 Staphylococcus aureus (B)

 10000 10000

 Pseudomonas aeruginosa (B)

 10000 10000

 Escherichia coli (B)

 10000 10000

 Enterobacter aerogenes (B)

 10000 10000

 Klebsiella pneumoniae (B)

 10000 10000

 Proteus vulgaris (B)

 10000 10000

 Pseudomonas oleovorans (B)

 10000 10000

 Bacteria (B), fungi (P) or yeast (H) investigated

 MHK of isosorbide dicaprilate [ppm] MHK of isosorbide [ppm]

 Citrobacter freundii (B)

 10000 10000

 Candida albicans (H)

 10000 10000

 Aspergillus brasiliensis (P)

 10000 10000

 Penicillium minioluteum (P)

 10000 10000

 Aspergillus terreus (P)

 10000 10000

 Fusarium solani (P)

 5000 10000

 Penicillium funicolosium (P)

 5000 10000

As can be seen from the results in Table 2, neither isosorbide nor isosorbide dicaprilate has an antimicrobial efficacy.

Due to the poor antimicrobial efficacy of the compounds of capnolic acid, isosorbide and dicaprilate of 5 isosorbide contained in the isosorbide caprylate composition 1 on the one hand, and to the antimicrobial efficacy of the composition "isosorbide caprylate 1" that follows from the results of Table 1, on the other hand, concludes that the isosorbide monocaprylate compound, also contained in the isosorbide caprylic composition 1, has significant antimicrobial efficacy, especially as a fungicide against yeasts and fungi.

For this reason, it is based on the fact that the insignificant activity of the isosorbide dicaprilate composition against the 10 Fusarium solani and Penicillium funicolosium fungi can be attributed to the isosorbide monocaprylate compound contained therein.

D) Application examples

The use according to the invention can take place, by way of example, in the following formulations.

Formulation example 1: revitalizing moisturizer

 Phase

 Substance of content% by weight

 Hostacerin® SFO 2.0

 Sunflower Seed Oil Sorbitol Esters

 Velsan® CCT 4,5

 Caprylic / capric triglycerides

 Cetiol® OE 4,5

 TO

 Dicaprilileter

 Phase

 Substance of content% by weight

 Lanette® 22 4.0

 Behenic alcohol

 Lanette® 18 4.0

 Steary alcohol

 Fucogel® 1000 1.0

 Biosacarid gum-1

 B

 Coenzyme® Q 10 0.1

 Ubiquinonas

 C

 Water up to 100

 Glycerin 10.0

 Hostaphat® CK 100 0.6

 Potassium Cetylphosphate

 D

 Phenoxyethanol 1.0

 Isosorbide Caprilate 1 1.0

 AND

 NaOH (10% by weight in water) qs.

Obtaining:

I mix the components of A and heat to 80 ° C,

II the components of C are mixed and heated to 80 ° C,

5 III adds B to I,

IV is added II to III and stirred until the mixture has cooled to room temperature,

V is added D to IV,

VI the pH value is adjusted with E to 5.5.

Formulation example 2:

 Phase

 Substance of content% by weight

 Hostacerin® EWO polyglyceryl-2-sesquiisoestearates (y) Alba wax (y) Carnauba wax (y) ethylhexyl stearate (y) magnesium stearate (y) magnesium stearate (y) aluminum stearate 16.0

 TO

 Isopropyl Palmitate 10.0

 Avocado oil

 2.0

 Velsan® CCT 2.5

 Caprylic / capric triglycerides

 Octopirox® 0.05

 B

 Piroctone Olamine

 Propylene Glycol 1.0

 C

 Water up to 100

 Glycerin 4.0

 Magnesium sulfate * 7 H2O 0.7

 0.5 Alantoma

 0.5 tocopheryl acetate

 Rosmarinus Officinalis (Rosemary) Leaf Oil 0.1

 D

 Urea 10.0

 Isosorbide Caprilate 1 1.0

 Phenoxyethanol 0.8

Obtaining:

I mix the components of A and heat to 80 ° C,

II the components of B are mixed until all substances are dissolved (eventually low

5 slight heating),

III is added II to I,

IV the components of C are mixed and heated to 50 ° C,

V is stirred IV with high speed until cooling to 35 ° C,

VI is added D at 35 ° C to V.

Formulation examples 3 and 4: phytosanitary formulations

 Form No.

 3. 4

 Content Substance

 Amount of substance of respective content [% by weight]

 Atrazine

 43.6 43.6

 Dispersogen® PSL 100

 - 1.7

 Genapol® LSS

 - 1.6

 Dispersogen® LFS

 2.1 -

 Propylene glycol

 4.3 4.3

 Defoamer® SE 57

 0.6 0.6

 Kelzan® S (2% by weight in water)

 7.3 7.3

 Isosorbide Caprilate 1

 0.3 0.2

 Blessed alcohol

 1.0 1.0

 Water

 up to 100 up to 100

5 Obtaining:

The active product is previously dispersed with the other substances of content (except the solution of Kelzan®S), and then it is subjected to a fine grinding, until the average particle size amounts to <2 micrometres. The solution of Kelzan®S is then introduced with stirring.

Formulation example 5: manual dishwashing detergent

 Content Substance

 % in weigh

 Hostapur® SAS 60 (alkanesulfonate, 60% by weight in water)

 40.0

 Hostapur® OS liquid (C14-16 sodium alkylsulfonate, 40% by weight in water)

 11.0

 Genaminox® LA (dimethyl lauramine oxide, 30% by weight in water)

 3.0

 Genagen® CAB (coco-amidopropyl betaine, 30% by weight in water)

 3.0

 Content Substance

 % in weigh

 Isosorbide Caprilate 1

 0.8

 Blessed alcohol

 0.8

 Water

 up to 100

Formulation example 6: surface cleaner (universal cleaner)

 Content Substance

 % in weigh

 Hostapur® SAS 60 (alkanesulfonate, 60% by weight in water)

 5.0

 Genapol® UD 080 (undecanol + 8 EO)

 2.0

 Genaminox® LA (dimethyl lauramine oxide, 30% by weight in water)

 2.0

 Methylisothiazolinone

 0.01

 Isosorbide Caprilate 1

 1.0

 Water

 up to 100

Obtaining formulation examples 5 and 6

5 Half of the amount of water is disposed, and the components are introduced with agitation in the order indicated in the tables indicated in the examples of formulations 5 and 6. Then the remaining amount of water is added further. Clear, aqueous compositions result.

Claims (14)

5 10 fifteen twenty 25 30 1.- Use of one or more of the compounds of the formula (I) image 1 where R is a linear or branched alkyl group with 5 to 11 carbon atoms, or a linear or branched, mono- or polyunsaturated alkenyl group, with 5 to 11 carbon atoms, as a fungicide 2. - Use according to claim 1, characterized in that the R moiety in the formula (I) is a saturated linear alkyl moiety with 7 to 9 carbon atoms. 3. - Use according to claim 2, characterized in that the R moiety in formula (I) is a linear alkyl moiety saturated with 7 carbon atoms. 4. - Use according to one or more of claims 1 to 3, characterized in that the compound or compounds of the formula (I) are used in a composition containing one or several different substances selected from the group consisting of sorbitol, esters of sorbitol, sorbitan, esters of sorbitan, isosorbide, diesters of isosorbide and carboxylic acids. 5. - Use according to claim 4, characterized in that the composition contains one or more compounds of the formula (I), and additionally I) isosorbide and II) one or more isosorbide diesters of the formula (II) image2 where R has the meaning indicated in formula (I). 6. - Use according to claim 4 or 5, characterized in that the composition contains one or more compounds of the formula (I), and additionally I) 0.05 to 0.7 parts by weight of isosorbide, and II) 0.1 to 1.0 parts by weight of one or more isosorbide diesters of the formula (II), respectively referred to 1.0 part by weight of the compound or compounds of the formula (I). 7. - Use according to one or several of claims 4 to 6, characterized in that the composition contains one or more compounds of the formula (I) and one or more sorbitan esters consisting of sorbitan and RaCOOH carboxylic acids, Ra being a group linear or branched alkyl, saturated, with 5 to 11 carbon atoms, or a linear or branched, mono- or polyunsaturated alkenyl group, with 5 to 11 carbon atoms, and the proportion 14 5 10 fifteen twenty 25 The weight of the compound or compounds of the formula (I) with respect to the sorbitan ester or the sorbitan esters also mentioned is from 70: 30 to 100: 0. 8. - Use according to claim 7, characterized in that the sorbitan ester or sorbitan esters consisting of sorbitan and RaCOOH carboxylic acids are selected from sorbitan esters constituted by sorbitan and caprylic acid. 9. - Use according to one or more of claims 4 to 8, characterized in that the OH index of the mixture of one or more compounds of the formula (I) and one or more compounds selected from the group consisting of sorbitol, esters of sorbitol, sorbitan, esters of sorbitan, isosorbide, diesters of isosorbide and carboxylic acids in the composition is less than or equal to 320. 10. - Use according to one or more of claims 4 to 9, characterized in that the composition contains the compound or compounds of the formula (I) in amounts of at least 30% by weight, respectively based on the total weight of the composition finished 11. - Use according to one or more of claims 1 to 10 in cosmetic, dermatological or pharmaceutical compositions, in phytosanitary formulations, in washing or cleaning agents, or in dyes or paints. 12. - Use according to claim 11, characterized in that the cosmetic, dermatological or pharmaceutical compositions, phytosanitary formulations, washing or cleaning agents, or dyes or paints, contain one or more compounds of the formula (I) in amounts from 0.01 to 10.0% by weight, referring respectively to the total weight of the finished cosmetic, dermatological or pharmaceutical compositions, phytosanitary formulations, washing or cleaning agents, or colorants or paints. 13. - Use according to claim 11 or 12, characterized in that the cosmetic, dermatological or pharmaceutical compositions, phytosanitary formulations, washing or cleaning agents, or dyes or paints, are constituted on an aqueous or aqueous-alcoholic basis, or they are presented as an emulsion or dispersion, and preferably as an emulsion. 14. - Use according to one or more of claims 11 to 13, characterized in that the cosmetic, dermatological or pharmaceutical compositions, phytosanitary formulations, washing or cleaning agents, or dyes or paints, have a pH value of 2 to 11.